4,4-Dimethyl-1-(oxiran-2-yl)pentan-3-one | 158871-18-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,4-Dimethyl-1-(oxiran-2-yl)pentan-3-one
• CAS: 158871-18-2
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: SVOPXWJRBSQBTF-UHFFFAOYSA-N

物化性质

• 沸点：
  215.2±13.0 °C(predicted)
• 密度：
  0.966±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  29.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,4-Dimethyl-1-(oxiran-2-yl)pentan-3-one 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 cis-1-[2-(hydroxymethyl)cyclopropyl]-2,2-dimethyl-1-propanone
  参考文献：
  名称：

  Diastereocontrol in the opening of vic-acceptor-donor cyclopropanes. Application to the synthesis of (cis) 1-EWG-2-hydroxymethylcyclopropanes

  摘要：

  Basic intramolecular ring opening reactions of vicinally substituted acceptor-donnor (trans)-cyclopropanes were studied. An application to the diastereoselective synthesis of (cis)-1-EWG-2-hydroxymethylcyclopropanes is presented.

  DOI：

  10.1016/s0040-4039(00)77266-2
• 作为产物：
  描述：

  2,2-dimethyl-6-hepten-3-one 在 氢氧化钾 、 N-溴代丁二酰亚胺(NBS) 、 水 作用下， 以 二甲基亚砜 为溶剂， 反应 0.08h， 生成 4,4-Dimethyl-1-(oxiran-2-yl)pentan-3-one
  参考文献：
  名称：

  A simple one-pot preparation of (Z)-cyclopropanes from γ,δ-ketoalkenes using KOH/DMSO intramolecular alkylation conditions.

  摘要：

  Sequential treatment of gamma,delta-ketoalkenes with aqueous NBS in DMSO and KOH as solid provides (Z)-cyclopropanes in good overall yields with a diastereoselective excess >99%.

  DOI：

  10.1016/s0040-4039(00)60138-7

文献信息

• A simple one-pot preparation of (Z)-cyclopropanes from γ,δ-ketoalkenes using KOH/DMSO intramolecular alkylation conditions.
  作者：Luc Dechoux、Maurice Ebel、Louis Jung、Jean Francois Stambach

  DOI：10.1016/s0040-4039(00)60138-7

  日期：1993.11

  Sequential treatment of gamma,delta-ketoalkenes with aqueous NBS in DMSO and KOH as solid provides (Z)-cyclopropanes in good overall yields with a diastereoselective excess >99%.
• Diastereocontrol in the opening of vic-acceptor-donor cyclopropanes. Application to the synthesis of (cis) 1-EWG-2-hydroxymethylcyclopropanes
  作者：Luc Dechoux、Eric Doris、Louis Jung、Jean François Stambach

  DOI：10.1016/s0040-4039(00)77266-2

  日期：1994.8

  Basic intramolecular ring opening reactions of vicinally substituted acceptor-donnor (trans)-cyclopropanes were studied. An application to the diastereoselective synthesis of (cis)-1-EWG-2-hydroxymethylcyclopropanes is presented.